5 Stick With HighRise Jeans (And Tuck In That Top!) I suspect there's a long, slouchy sweater somewhere that I *could* wear with my updated tall boots and skinny jeansbut it would require a halftuck (to show off that waist) in order to keep the look current A much safer bet, for sure, is go all in on the highriseSmooth leather or suede that reaches from toe to knee They can have buckles or straps, are typically zippered, and come in a variety of colors, from your standard black and brown to tan, green, burgundy, and navy Casual flat knee high boots with jeans